Process for producing fluorinated methyl-benzyl alcohol

ABSTRACT

An object of the present invention is to provide a process for producing a fluorinated methyl-benzyl alcohol, which process is industrially practicable.  
     A process for producing a fluorinated methyl-benzyl alcohol according to the present invention comprises hydrogenolysis of one hydroxyl group in fluorinated benzene dimethanol.

CROSS REFERENCE OF RELATED APPLICATION

[0001] This application is an application filed under 35 U.S.C. §111(a)claiming benefit pursuant to 35 U.S.C. §119(e) of the filing date ofProvisional Application No. 60/256,918 filed on Dec. 21, 2000, pursuantto 35 U.S.C. §111(b).

DETAILED DESCRIPTION OF THE INVENTION

[0002] 1. Technical Field

[0003] The present invention relates to a process for producingfluorinated methyl-benzyl alcohols by hydrogenolysis of one hydroxylgroup in a fluorinated benzene dimethanol, particularly byhydrogenolysis in a solvent in the presence of a catalyst. Fluorinatedmethyl-benzyl alcohols are useful as a starting material or anintermediate of medical and pharmaceutical products, agriculturalchemicals or other organic compounds. For example, JP-B-1-20143/1989discloses that fluorinated methyl-benzyl alcohols are reacted withcyclopropane carboxylic acids to obtain ethers having high insecticidalactivities.

[0004] 2. Background Art

[0005] For example, the following processes are proposed as the processfor producing fluorinated methyl-benzyl alcohols.

[0006] 1) JP-B-4-6694/1992 discloses a process for producing4-methyl-2,3,5,6-tetrafluorobenzyl alcohol by reducing4-methyl-2,3,5,6-tetrafluorobenzoic acid with lithium aluminum hydridein dried ether, and a process for producing3-methyl-2,4,5,6-tetrafluorobenzyl alcohol by reducing3-methyl-2,4,5,6-tetrafluorobenzaldehyde with sodium borohydride inmethanol.

[0007] 2) JP-A-63-77829/1988 discloses a process for producing2-methyl-3,4,5,6-tetrafluorobenzyl alcohol by allowing pentafluorobenzylalcohol to react with magnesium methyl bromide in tetrahydrofurane.

[0008] 3) DE-B-3714602 discloses a process for producing4-methyl-2,3,5,6-tetrafluorobenzyl alcohol by reducing4-methyl-2,3,5,6-tetrafluoro benzoic acid with sodium borohydride in1,2-dimethoxyethane.

[0009] 4) GB-B-2155464 discloses a process for producing4-methyl-2,3,5,6-tetrafluorobenzyl alcohol by reducing4-methyl-2,3,5,6-tetrafluorobenzoic acid chloride with sodiumborohydride.

[0010] However, these processes are not favorable for carrying outindustrially because of having problems in that expensive reducingagents are used and strict moisture control for these reducing agents isrequired.

[0011] Object of the Invention

[0012] Accordingly, it is an object of the invention to provide aprocess for producing a fluorinated methyl-benzyl alcohol, which processcan be carried out industrially.

[0013] Means to Solve the Problems

[0014] The present invention comprises the following subjects.

[0015] [1] A process for producing a fluorinated methyl-benzyl alcoholrepresented by formula (2):

[0016] (wherein m represents an integer of 0 to 3, n represents aninteger of 1 to 4, and m+n is an integer of 1 to 4), which processcomprises hydrogenolysis of one hydroxyl group in a fluorinated benzenedimethanol represented by formula (1):

[0017] (wherein m and n are the same as above).

[0018] [2] The process for producing a fluorinated methyl-benzyl alcoholas described in [1], wherein the fluorinated benzene dimethanol isrepresented by formula (3)

[0019] (wherein n represents an integer of 1 to 4), and thecorresponding fluorinated methyl-benzyl alcohol is represented byformula (4)

[0020] (n is the same as above).

[0021] [3] The process for producing a fluorinated methyl-benzyl alcoholas described in [1], wherein the fluorinated benzene dimethanol istetrafluorobenzene dimethanol represented by formula (5)

[0022] and the corresponding fluorinated methyl-benzyl alcohol istetrafluoromethyl-benzyl alcohol represented by formula (6)

[0023] [4] The process for producing a fluorinated methyl-benzyl alcoholas described in [3], wherein the tetrafluorobenzene dimethanol of theformula (5) is 2,3,5,6-tetrafluorobenzene-1,4-dimethanol and thetetrafluoromethyl-benzyl alcohol of the formula (6) is2,3,5,6-tetrafluoro-4-methyl-benzyl alcohol.

[0024] [5] The process for producing a fluorinated methyl-benzyl alcoholas described in any one of [1] to [4], wherein the hydrogenolysis iscarried out in a solvent in the presence of a catalyst.

[0025] [6] The process for producing a fluorinated methyl-benzyl alcoholas described in [5], wherein the catalyst comprises at least one metalselected from cobalt, iron, copper, nickel, platinum, palladium andrhenium, and the hydrogenolysis is carried out using hydrogen.

[0026] [7] The process for producing a fluorinated methyl-benzyl alcoholas described in [6], wherein the catalyst is at least one catalystselected from the group consisting of a sponge cobalt catalyst, amodified sponge cobalt catalyst, a sponge nickel catalyst and a modifiedsponge nickel catalyst.

[0027] [8] The process for producing a fluorinated methyl-benzyl alcoholas described in [6], wherein the catalyst is a sponge cobalt catalyst ora modified sponge cobalt catalyst.

[0028] [9] The process for producing a fluorinated methyl-benzyl alcoholas described in [6], wherein the catalyst is a supported cobaltcatalyst, a supported nickel catalyst, a supported palladium catalyst ora supported rhenium catalyst.

[0029] [10] The process for producing a fluorinated methyl-benzylalcohol as described in any one of [5] to [9], wherein the solvent is asingle or mixed solvent comprising at least one selected from saturatedaliphatic or alicyclic hydrocarbon, aromatic hydrocarbon, alcoholicsolvent, ether of aliphatic or alicyclic hydrocarbon and water.

[0030] [11] The process for producing a fluorinated methyl-benzylalcohol as described in [10], wherein the solvent is a single or mixedsolvent comprising at least one selected from toluene, xylene, methanol,ethanol, dioxane, dioxolane and water.

[0031] [12] The process for producing a fluorinated methyl-benzylalcohol as described in any one of [1] to [11], wherein thehydrogenolysis reaction is carried out in a hydrogen partial pressure offrom 0.05 to 15 MPa.

[0032] [13] The process for producing a fluorinated methyl-benzylalcohol as described in any one of [5] to [12], wherein the amount ofthe solvent used in the hydrogenolysis reaction is 1 to 20 times by massbased on the fluorinated benzene dimethanol.

[0033] [14] The process for producing a fluorinated methyl-benzylalcohol as described in any one of [6] to [13], wherein the amount ofhydrogen used in the hydrogenolysis reaction is 100 to 180% by molebased on the fluorinated benzene dimethanol.

[0034] Mode for Carrying Out the Invention

[0035] The present invention is described in detail below.

[0036] The present invention relates to a process for producingfluorinated methyl-benzyl alcohols by hydrogenolysis of one hydroxylgroup in fluorinated benzene dimethanol, particularly, hydrogenolysis ina solvent in the presence of a catalyst.

[0037] The fluorinated benzene dimethanol used as a starting material inthe invention can be synthesized by known methods. For example,tetrafluorobenzene dimethanol can be easily prepared by hydrolysis of2,3,5,6-tetrafluorobenzene dimethanol diacetate, as described inJP-A-1-238555/1989.

[0038] As the catalyst used in the invention, metal catalysts arefavorable, particularly, a catalyst comprising at least one metalselected from cobalt, iron, copper, nickel, platinum, palladium andrhenium is more favorable.

[0039] The catalyst used may be a metal itself, a sponge metal catalystor a supported catalyst.

[0040] The “sponge metal catalyst” used in the present invention is aporous metal catalyst obtainable from an alloy which comprises a metalinsoluble in alkali or acid such as nickel or cobalt, and a metalsoluble in alkali or acid such as aluminum, silicon, zinc or magnesiumto thereby eluting a metal soluble in alkali or acid by use of alkali oracid.

[0041] In the present invention, it is preferred to use the spongecobalt catalyst and sponge nickel catalyst.

[0042] Further, a modified sponge metal catalyst obtainable bymodification in the presence of a metal other than nickel or cobalt, ora metal oxide thereof may be used in the present invention. Examplesthereof may include a modified sponge nickel catalyst modified withmolybdenum and a modified sponge cobalt catalyst modified withmanganese.

[0043] The “supported catalyst” used in the present invention is acatalyst supporting a highly dispersed fine divided metal containing atleast one metal species or metal oxide particles on a carrier such assilica, alumina, silica alumina, activated charcoal or diatomaceousearth.

[0044] It is preferred to use a supported cobalt catalyst, supportediron catalyst, supported copper catalyst, supported nickel catalyst,supported platinum catalyst, supported palladium catalyst and supportedrhenium catalyst in the present invention.

[0045] In particular, it is preferred to use the supported cobaltcatalyst, the supported nickel catalyst, the supported palladiumcatalyst and the supported rhenium catalyst.

[0046] Further, a supported catalyst, which comprises, as a maincomponent, at least one metal selected from cobalt, iron, copper,nickel, platinum, palladium and rhenium, further modified by adding atleast one of the above metal species or other metal species can be usedin the present invention. Examples thereof may include a supportednickel-copper-alumina catalyst, supported copper-chromium-silicacatalyst, supported palladium-rhenium-alumina catalyst and supportednickel-cobalt-alumina catalyst.

[0047] Next, the hydrogenolysis reaction of the invention will bedescribed.

[0048] The amount of the catalyst added in the reaction is notparticularly limited, and differs depending to the catalyst form.Generally, the catalyst is used in an amount of from 0.01 to 300% bymass, preferably 0.05 to 100% by mass, particularly preferably 0.1 to50% by mass based on fluorinated benzene dimethanol subjected to thehydrogenolysis.

[0049] Preferable examples of the solvent used in the hydrogenolysisreaction according to the present invention may include saturatedaliphatic and alicyclic hydrocarbons, aromatic hydrocarbons, alcohols,ethers of aliphatic and alicyclic hydrocarbons and water. Examples ofthe saturated aliphatic and alicyclic hydrocarbons include n-hexane,n-octane, iso-octane and cyclohexane; examples of the aromatichydrocarbons include benzene, toluene and xylene; examples of alcoholsinclude methanol, ethanol, n-propanol, isopropanol, n-butanol,ethyleneglycol and propyleneglycol; and examples of ethers aliphatic andalicyclic hydrocarbons include diethylether, diisopropylether,methyl-tertiary-butylether, tetrahydrofuran, dioxane and dioxolane.These solvents may be used singly or in a mixed one containing any ofthese solvents. Further, in the case of using at least two solvents as amixed solvent, non-uniformly mixed solvents can be used. Preferableexamples of the single solvent are toluene, methanol and dioxane, andpreferable examples of the mixed solvent are toluene-methanol,toluene-water, toluene-methanol-water and dioxane-water. The solvent isused in an amount of from 0.5 to 30 times by mass, preferably 1 to 20times by mass based on tetrafluorobenzene dimethanol.

[0050] The hydrogenolysis of the present invention can be carried out byintroducing hydrogen into gas phase thereby heating to predeterminedtemperature, or by purging gas phase with inert gas that has no effecton the hydrogenolysis reaction, and heating to predetermined temperaturethereby introducing hydrogen. The reaction can be carried out at atemperature of from ordinary temperature to 250° C., preferably abovethe temperature at which the fluorinated benzene dimethanol is melting,or dissolving in the solvent. The pressure for the hydrogenolysisreaction is appropriately from 0.05 to 15 MPa by the partial pressure ofhydrogen. The hydrogen gas used in the present reaction does not havenecessarily a high purity, and may contain inert gases that have noeffect on the hydrogenolysis reaction especially.

[0051] The fluorinated benzene methanol used as a starting materialaccording to the present invention is a compound represented by theabove formula (1). Examples thereof may include monofluorobenzenedimethanols (such as 2-fluorobenzene-1,4-dimethanol), difluorobenzenedimethanols (such as 2,3-difluorobenzene-1,4-dimethanol,2,5-difluorobenzene-1,4-dimethanol, 3,5-difluorobenzene-1,4-dimethanol),trifluorobenzene dimethanols (such as2,3,5-trifluorobenzene-1,4-dimethanol), tetrafluorobenzene dimethanols(such as 3,4,5,6-tetrafluorobenzene-1,2-dimethanol,2,4,5,6-tetrafluorobenzene-1,3-dimethanol,2,3,5,6-tetrafluorobenzene-1,4-dimethanol), monochloro-monofluorobenzenedimethanols (such as 6-chloro-2-fluorobenzene-1,4-dimethanol),monochloro-difluorobenzene dimethanols (such as2,3-difluoro-5-chlorobenzene-1,4-dimethanol),monochloro-trifluorobenzene dimethanols (such as2,3,5-trifluoro-6-chlorobenzene-1,4-dimethanol), anddichloro-difluorobenzene dimethanols (such as2,6-difluoro-4,5-dichlorobenzene-1,4-dimethanol).

[0052] Preferable examples are tetrafluorobenzene dimethanols (such as3,4,5,6-tetrafluorobenzene-1,2-dimethanol,2,4,5,6-tetrafluorobenzene-1,3-dimethanol,2,3,5,6-tetrafluorobenzene-1,4-dimethanol), and a more preferableexample is 2,3,5,6-tetrafluorobenzene-1,4-dimethanol.

[0053] The fluorinated methyl-benzyl alcohol obtainable by theproduction process of the present invention is represented by the aboveformula (2) and corresponds to a compound obtainable by hydrogenolysisof one hydroxy group in the fluorinated benzene dimethanol of theformula (1). Examples of the fluorinated methyl-benzyl alcohol mayinclude preferably tetrafluoro-methyl-benzyl alcohols (such as3,4,5,6-tetrafluoro-2-methyl-benzyl alcohol,2,4,5,6-tetrafluoro-3-methyl-benzyl alcohol and2,3,5,6-tetrafluoro-4-methyl-benzyl alcohol), and more preferably2,3,5,6-tetrafluoro-4-methyl-benzyl alcohol.

[0054] The fluorinated methyl-benzyl alcohol obtained by the productionprocess of the present invention may be purified by separating thecatalyst by filtration, centrifugation and other operations, thenconcentration, extraction and/or distillation.

[0055] Effect of the Invention

[0056] According to the present invention, fluorinated methyl-benzylalcohols, especially tetrafluoromethyl-benzyl alcohol can be produced byan industrially advantageous method.

EXAMPLES

[0057] The present invention will be described with reference to thefollowing examples hereinafter, but it is not restricted by theexamples.

Example 1

[0058] To a 1 liter autoclave, 300 ml of toluene, 25 g of a spongecobalt catalyst in a water-containing state (in which the catalystamount is 5 g) and 30 g of 2,3,5,6-tetrafluorobenzene-1,4-dimethanolwere charged and a gas phase was thoroughly purged with hydrogen, andthereafter the hydrogen pressure was set to 1.5 MPa at ordinarytemperature (the pressure means gauge pressure hereinafter). Thestirring and heating for the autoclave were started and the temperaturethereof was kept to 160° C. When the temperature reached to 160° C., thepressure was 2.2 MPa. The reaction was continued for 1 hr. Then, theautoclave was cooled to room temperature. After the cooling, thepressure showed 1.0 MPa. At this time, the amount of absorbed hydrogenwas 104 mol % based on 2,3,5,6-tetrafluorobenzene-1,4-dimethanolcharged. Hydrogen inside a reactor was removed, and thereafter thereaction mixture was recovered and the catalyst was filtered.

[0059] The reaction mixture was heated under reduced pressure to removethe solvent by distillation, and further by gradually decreasing thepressure, a fraction distilled at 665 Pas at a temperature of from 100to 105° C. was recovered. The fraction was analyzed with nuclearmagnetic resonance spectrum (NMR) analysis and gas chromatography-massspectroscopy (GC-MS) to identify 98% 2,3,5,6-tetrafluoro-4-methyl-benzylalcohol.

[0060] Further, using the distilled 2,3,5,6-tetrafluoro-4-methyl-benzylalcohol as an authentic sample, a part of the reaction mixture recoveredin the above reaction was analyzed with the gas chromatography internalstandard method. In result, the conversion of2,3,5,6-tetrafluorobenzene-1,4-dimethanol was 94%, the yield of2,3,5,6-tetrafluoro-4-methyl-benzyl alcohol was 88% (on the basis of2,3,5,6-tetrafluorobenzene-1,4-dimethanol), and the yield of2,3,5,6-terafluoro-p-xylene was 4% (on the basis of2,3,5,6-tetrafluorobenzene-1,4-dimethanol).

Example 2

[0061] To a 100 ml autoclave, 30 ml of 1,4-dioxane, 2.5 g of a spongecobalt catalyst in a water-containing state (in which the catalystamount is 0.5 g) and 3.0 g of 2,3,5,6-tetrafluorobenzene-1,4-dimethanolwere charged and a gas phase was thoroughly purged with hydrogen, andthereafter the hydrogen pressure was set to 0.3 MPa at ordinarytemperature. The stirring and heating for the autoclave were started andthe temperature thereof was kept to 160° C. When the temperature reachedto 160° C., the pressure was 0.5 MPa. Hydrogen was fed to the autoclaveto keep a pressure at 0.5 MPa, and when the hydrogen absorbing amountreached to 145 mol % based on 2,3,5,6-tetrafluorobenzene-1,4-dimethanolcharged while watching the hydrogen flow rate, the reaction was stopped.The reaction required 4 hr.

[0062] Then, the autoclave was cooled to room temperature. Hydrogeninside a reactor was removed, and thereafter the reaction mixture wasrecovered and the catalyst was filtered.

[0063] The resulting reaction mixture was analyzed with the gaschromatography internal standard method. In result, the conversion of2,3,5,6-tetrafluorobenzene-1,4-dimethanol was 69%, the yield of2,3,5,6-tetrafluoro-4-methyl-benzyl alcohol was 40% (on the basis of2,3,5,6-tetrafluorobenzene-1,4-dimethanol), and the yield of2,3,5,6-terafluoro-p-xylene was 7% (on the basis of2,3,5,6-tetrafluorobenzene-1,4-dimethanol).

Example 3

[0064] To a 100 ml autoclave, 30 ml of 1,4-dioxane, 3.0 g of a supportedpalladium-carbon catalyst and 3.0 g of2,3,5,6-tetrafluorobenzene-1,4-dimethanol were charged and a gas phasewas thoroughly purged with hydrogen, and thereafter the hydrogenpressure was set to 5 MPa at ordinary temperature. The stirring andheating for the autoclave were started and the temperature thereof waskept to 220° C. When the temperature reached to 220° C., the pressurewas 9 MPa. The reaction continued for 12 hr. Then, the autoclave wascooled to room temperature and the pressure after the cooling showed 4.7MPa. At this time, the amount of absorbed hydrogen was 82 mol % based on2,3,5,6-tetrafluorobenzene-1,4-dimethanol charged.

[0065] Hydrogen inside a reactor was removed, and thereafter thereaction mixture was recovered and the catalyst was filtered. Theresulting reaction mixture was analyzed with the gas chromatographyinternal standard method. In result, the conversion of2,3,5,6-tetrafluorobenzene-1,4-dimethanol was 56%, the yield of2,3,5,6-tetrafluoro-4-methyl-benzyl alcohol was 37% (on the basis of2,3,5,6-tetrafluorobenzene-1,4-dimethanol), and the yield of2,3,5,6-terafluoro-p-xylene was 6% (on the basis of2,3,5,6-tetrafluorobenzene-1,4-dimethanol).

Example 4

[0066] To a 100 ml autoclave, 30 ml of 1,4-dioxane, 1.5 g of a supportedrhenium oxide-alumina catalyst and 3.0 g of2,3,5,6-tetrafluorobenzene-1,4-dimethanol were charged and a gas phasewas thoroughly purged with hydrogen, and thereafter the hydrogenpressure was set to 3 MPa at ordinary temperature. The stirring andheating for the autoclave were started and the temperature thereof waskept to 220° C. When the temperature reached to 220° C., the pressurewas 4.8 MPa. The reaction continued for 5 hr.

[0067] Then, the autoclave was cooled to room temperature and thepressure after the cooling showed 2.6 MPa. At this time, the amount ofabsorbed hydrogen was 116 mol % based on2,3,5,6-tetrafluorobenzene-1,4-dimethanol charged. Hydrogen inside areactor was removed, and thereafter the reaction mixture was recoveredand the catalyst was filtered. The resulting reaction mixture wasanalyzed with the gas chromatography internal standard method. Inresult, the conversion of 2,3,5,6-tetrafluorobenzene-1,4-dimethanol was83%, the yield of 2,3,5,6-tetrafluoro-4-methyl-benzyl alcohol was 58%(on the basis of 2,3,5,6-tetrafluorobenzene-1,4-dimethanol), and theyield of 2,3,5,6-terafluoro-p-xylene was 14% (on the basis of2,3,5,6-tetrafluorobenzene-1,4-dimethanol).

Example 5

[0068] To a 1 liter autoclave, 600 ml of toluene, 30 g of a spongecobalt catalyst in a water-containing state (in which the catalystamount is 6 g) and 60 g of 2,3,5,6-tetrafluorobenzene-1,4-dimethanolwere charged and gas phase was thoroughly purged with nitrogen. Thestirring and heating for the autoclave were started and the temperaturethereof was kept to 160° C. The pressure at this time was 0.28 MPa.Hydrogen was charged to the autoclave to increase the pressure to 0.53MPa. Then, hydrogen was further fed to the autoclave to keep thepressure at 0.53 MPa, and when the hydrogen absorbing amount reached to130 mol % based on 2,3,5,6-tetrafluorobenzene-1,4-dimethanol chargedwhile watching the hydrogen flow rate, the reaction was stopped. Thereaction required 30 minutes.

[0069] Then, the autoclave was cooled to room temperature, gases insidethe reactor were removed, and thereafter the reaction mixture wasrecovered and the catalyst was filtered.

[0070] The resulting reaction mixture was analyzed with the gaschromatography internal standard method. In result, the conversion of2,3,5,6-tetrafluorobenzene-1,4-dimethanol was 99.5%, the yield of2,3,5,6-tetrafluoro-4-methyl-benzyl alcohol was 82% (on the basis of2,3,5,6-tetrafluorobenzene-1,4-dimethanol), and the yield of2,3,5,6-tetrafluoro-p-xylene was 11% (on the basis of2,3,5,6-tetrafluorobenzene-1,4-dimethanol).

1. A process for producing a fluorinated methyl-benzyl alcoholrepresented by formula (2):

(wherein m represents an integer of 0 to 3, n represents an integer of 1to 4, and m+n is an integer of 1 to 4), which process compriseshydrogenolysis of one hydroxyl group in a fluorinated benzene dimethanolrepresented by formula (1):

(wherein m and n are the same as above).
 2. The process for producing afluorinated methyl-benzyl alcohol according to claim 1, wherein thefluorinated benzene dimethanol is represented by the formula (3)

(wherein n represents an integer of 1 to 4), and the correspondingfluorinated methyl-benzyl alcohol is represented by formula (4):

(wherein n is the same as above).
 3. The process for producing afluorinated methyl-benzyl alcohol according to claim 1, wherein thefluorinated benzene dimethanol is tetrafluorobenzene dimethanolrepresented by formula (5)

and the corresponding fluorinated methyl-benzyl alcohol istetrafluoromethyl-benzyl alcohol represented by formula (6)


4. The process for producing a fluorinated methyl-benzyl alcoholaccording to claim 3, wherein the tetrafluorobenzene dimethanol of theformula (5) is 2,3,5,6-tetrafluorobenzene-1,4-dimethanol and thetetrafluoro-methyl-benzyl alcohol of the formula (6) is2,3,5,6-tetrafluoro-4-methyl-benzyl alcohol.
 5. The process forproducing a fluorinated methyl-benzyl alcohol according to any one ofclaims 1 to 4, wherein hydrogenolysis is carried out in a solvent in thepresence of a catalyst.
 6. The process for producing a fluorinatedmethyl-benzyl alcohol according to claim 5, wherein the catalystcomprises at least one metal selected from cobalt, iron, copper, nickel,platinum, palladium and rhenium, and hydrogenolysis is carried out usinghydrogen.
 7. The process for producing a fluorinated methyl-benzylalcohol according to claim 6, wherein the catalyst is at least onecatalyst selected from the group consisting of a sponge cobalt catalyst,a modified sponge cobalt catalyst, a sponge nickel catalyst and amodified sponge nickel catalyst.
 8. The process for producing afluorinated methyl-benzyl alcohol according to claim 6, wherein thecatalyst is a sponge cobalt catalyst or a modified sponge cobaltcatalyst.
 9. The process for producing a fluorinated methyl-benzylalcohol according to claim 6, wherein the catalyst is a supported cobaltcatalyst, a supported nickel catalyst, a supported palladium catalyst ora supported rhenium catalyst.
 10. The process for producing afluorinated methyl-benzyl alcohol according to any one of claims 5 to 9,wherein the solvent is a single or mixed solvent comprising at least oneselected from saturated aliphatic or alicyclic hydrocarbon, aromatichydrocarbon, alcoholic solvent, ether of aliphatic or alicyclichydrocarbon and water.
 11. The process for producing a fluorinatedmethyl-benzyl alcohol according to claim 10, wherein the solvent is asingle or mixed solvent comprising at least one selected from toluene,xylene, methanol, ethanol, dioxane, dioxolane and water.
 12. The processfor producing a fluorinated methyl-benzyl alcohol according to any oneof claims 1 to 11, wherein the hydrogenolysis reaction is carried out ina hydrogen partial pressure of from 0.05 to 15 MPa.
 13. The process forproducing a fluorinated methyl-benzyl alcohol according to any one ofclaims 5 to 12, wherein the amount of the solvent used in thehydrogenolysis reaction is 1 to 20 times by mass based on thefluorinated benzene dimethanol.
 14. The process for producing afluorinated methyl-benzyl alcohol according to any one of claims 6 to13, wherein the amount of hydrogen used in the hydrogenolysis reactionis 100 to 180% by mole based on the fluorinated benzene dimethanol.